Bill Cunningham New York is a film not quite as compelling as its subject. Following eccentric New York Times fashion photographer Bill Cunningham as he attends fashion shows, covers society events, and films average men and women on the streets of the Big Apple, it takes a scattered approach to his life, showing us snippets without a strong guiding focus. What is most interesting about him is his egalitarian approach to clothing. Anything that can’t be worn in normal life doesn’t interest him, and wild styles and colors excite him. He values creativity above all else and prefers the delightfully gaudy to the rigidly presentable. Watching him work made me want to dress more boldly, and as a New Yorker I now find myself hoping to be photographed by him, because if you can catch his eye, you’ve really got something.

Various developments in his life are fascinating. He celebrated his eightieth birthday during the production of this film and spent many of those years living in a shoebox studio in Carnegie Hall, until he and his fellow remaining artists were evicted; we hear a few stories of what life was like in this unique artistic oasis, but could do with greater detail. He left Women’s Wear Daily after his editors changed his copy to insult the subjects of his photos; such judgmental fashion commentary is anathema to him. Eventually, he was made an Officer of Arts and Letters by the French Ministry of Culture, an honor he seemed genuinely gratified but baffled by; even though he was the guest of honor, he worked the event like any other.

Late in the film, first-time feature director Richard Press touches on emotional subjects that start to give us a deeper glimpse into the smiling, infectious man. When asked about his romantic history, Cunningham claims he never had time for one, but vaguely admits to having normal human urges. Is he gay? That was a matter of some concern to his parents, he tells us, but he doesn’t give us a definitive answer one way or the other. Is religion important to him? Here Cunningham remains silent for a long period before answering, and we sense a nerve being struck. Press is polite and even apologetic when asking such personal questions, and who could blame him for not wanting to offend such a generous, unassuming man, but he holds back precisely where he should push further. The talking heads have nothing but nice things to say about Bill Cunningham, but who is he really?

Conan O'Brien, legally prohibited from being funny on TV

Conan O’Brien Can’t Stop is also about an artist, but even though the title entertainer works in comedy, it’s a darker, deeper, and more revealing film. It takes place after Conan O’Brien was forcibly evicted from NBC’s The Tonight Show, which he hosted for only seven months. I remember during that time, when he was in a nasty public battle with the network and late-night lead-in-turned-rival Jay Leno, he unleashed the angriest, most lacerating comedy I’ve seen from him, and it was some of the finest work he’d ever done. A condition of his settlement with NBC required him not to appear on television for six months, so instead he launched The Legally Prohibited from Being Funny on Television live national tour, which seems to have been more an act of need than of PR savvy; the man is at a loss without an audience to play to.

The Conan O’Brien we meet on the road is brittle, tired, overextended. I hear stories sometimes of celebrities treated for “exhaustion” and assume it’s just publicist-speak for rehab, but with O’Brien I’d believe it. He is generous with his time, unwilling to slight his fans, but also resentful of those fans for demanding what little energy he has left. In this frustrated state he belittles his friends and coworkers with passive-aggressive sarcasm, though sometimes it’s just aggressive-aggressive; a visit from Jack McBrayer, who currently co-stars on NBC’s 30 Rock but used to appear in comedy bits on O’Brien’s Late Night talk show, is met with such abject meanness (disguised as friendly ribbing) that McBrayer appears stunned. Whether McBrayer is in on the joke is hard to say, but if I were in on that kind of joke, I’d want to get out of it.

The most fascinating insight of director Rodman Flender‘s film is right there in the title: Conan O’Brien can’t stop. To watch him on television or on stage is to laugh, but to watch him behind the scenes is to be exhausted with him. Even when his only audience is his assistant Sona or a flight attendant on a private plane, he is unable, or unwilling, to turn off the impulse to entertain and to receive the approval of laughter or applause. Watching him gave me the impression that a nightly talk show serves as his pressure release valve, providing an outlet for this need while also anchoring him in a consistent routine that, I can only hope, keeps him sane enough to spare those around him.